Youth with a history of out-of-home placement are overrepresented among young adults who end up on the streets. What could be viewed as a failure by some is experienced as an opportunity by others: youth’s lived experience of the streets is shaped by what they’ve known prior to arriving on the streets. The goal of this research was to fill a gap in our knowledge around the connection between the lived experience of out-of-home care and the lived experience of homelessness among youth. Using the method of récits de vie, I met with six young people who were living on the streets and, as children or adolescents, had been removed from their families to be placed in out-of-home care under youth protection laws in Quebec (Canada). Their life trajectories were studied through the lens of “vulnerabilisation”: a process leading to both material impoverishment and relegation to an unfavourable social position. While in care, the young people in my study experienced three forms of vulnerabilisation: weakening of family ties, professional and social disqualification, and stigmatisation. The youth responded to these processes by accepting and identifying with their vulnerable status, by refusing or negating this status, or by rationalizing and negotiating their status. This study helps us better understand how the experience of out-of-home care and street life are connected in young people’s lives. My results could support further studies, as well as inform practices with this specific population.